58 and a Half Hours/September 9, 2016
“God, Vampire Knight is so pretentious! They should have given up after the first season!” Megumi said loudly. “Yeah, I wasn't too fond of it either,” Valen said.
Turns out Megumi was only shy around new people; once you drew her out of her shell, she was actually quite loud and opinionated. Today for lunch she was sitting at the same table as Yuu, Valen, Minako, and Cupcake. Like usual, nobody could figure out where the junk food Cupcake was eating came from.
“So what have you watched lately?” Yuu asked. “I know you were drawing that Trigun picture a few days ago, but that's older than we are.”
“Well, I went through a bit of an Oreimo kick lately,” Megumi said. “What's that about?” Minako asked. “Well, it's about a guy who finds out that his little sister is a huge fan of little sister themed eroge...”
“Huh,” Minako said, trying to sound disinterested. Yuu might have been able to catch the slight twinkle in her eye that would have given her away, if he hadn't been approached right then.
“Please excuse the intrusion,” Ami said, as she tapped Yuu's shoulder. He turned to look, and standing with her was Manami. “Excuse me for a moment,” Yuu said to the girls at his table, standing up to face Ami and Manami. Megumi carried on talking to Megumi and Valen.
“What can I do for you?” Yuu asked cheerfully. “We just kind of wanted to meet the class hero,” Ami said, with a small trace of embarrassment in her voice. “And to thank you for saving Nanami,” Manami added. “It wasn't just me,” Yuu said, bashfully. “I would never have found her in time if not for Minako.”
“Don't downplay your role in saving her,” Manami said, seriously. “Erina shared the story with us, and Nanami would not be alive if not for you.”
“Do you know Nanami?” Yuu asked.
“We've met her a few times, years ago,” Ami said. “Our parents ran in the same social circles until that unfortunate accident. May I ask how you know her?”
“We've gone to the same school for the last several years. That's how I know Erina as well,” Yuu said.
“Well, if there's anything you ever need, feel free to ask,” Ami said. After a half moment of hesitation, Yuu asked, “Would you two care to sit with us? We can pull that table there over to extend this one.”
“It would be rude to decline your invitation,” Manami said, as Yuu moved and slid a nearby table over. As the three sat down, Yuu noticed that Erina had joined the other girls at the table while he was standing.
“Hey Erina, any news with Nanami?” Yuu asked.
“The hospital's holding her for observation until Sunday, so she should be making it back Monday,” Erina answered.
The rest of the lunch period passed as everyone made small talk with each other.
“Alright, everyone; Ms. Nakajou is already waiting for you all out in the field behind the school. It's not like this is a very large school so I don't doubt you'll have an easy time finding the locker rooms to change,” Dianne announced. As everyone in the classroom started to stand up, she added, “Yuu, I'm going to need you to stay in here for a few minutes.”
No one noticed the sigh of relief that came from the back of the classroom, as everyone besides Yuu filed out of the classroom.
Once everyone had left the room, Dianne approached Yuu's desk. “We need to have a little talk,” she said.
“Why didn't you tell me you were going to skip class yesterday?” Dianne asked.
“I... guess I don't have a good answer for that,” Yuu said. “It was kind of spur of the moment.”
“Still, you could have come and told me. Truthfully, I was starting to get worried about Nanami too,” Dianne said.
“So... am I in trouble?” Yuu asked, apologetically.
“Not at the moment,” Diane said, crossing her arms. “But we need to be able to trust each other, especially if you want to have a romantic relationship with me at some point in the future. If you had come to me and asked yesterday, I would have excused you, given what you were doing.”
“Why don't Minako and Erina get a lecture?” Yuu asked.
“They will, I just wanted to speak to you alone because of the unusual dynamic of our relationship.” Dianne unfolded her arms, moved over to Yuu, and put her arm around his shoulders. “Look, I'm going to trust that you won't ask to be excused for anything frivolous. You need to trust me enough to tell me about it.”
“Okay, I'll be sure to do that in the future,” Yuu said.
“Alright, now go get changed for P.E. and head on out with everyone else.”
It was the first time Yuu had gone in the locker room; the lack of gym class so far this week had not given him any reason to come in yet. While it was relatively small, it was larger than he expected it to be, with about ten lockers and a small open shower area in the back. 'I guess the design makes sense,' Yuu thought, 'this building would be a huge sunk cost if Nanami didn't intend to run it as a normal school once we graduate...' Yuu picked a locker at random, opened it, and tossed his bag on the bench nearby.
While Yuu was hurriedly trying to change, he heard the door to the locker room open and close. Still in his boxer shorts, he turned his head towards the entrance as he hurriedly shoved his other clothes into the locker. He saw a woman who looked to be in her early twenties walk around the privacy wall. She had red hair that ran to the middle of her back, and was dressed in black lingerie; she tossed the button-up shirt and pencil skirt she was holding off to the side as she got into the room proper.
As she quickly strode across the room, Yuu tried to speak through his surprise. “Who the... what are you doing h...?” he started, but was silenced as she put a finger up to his lips. He wasn't able to get anything else out once she removed her finger as she got down on her knees with surprising swiftness and pulled his boxers down with a quick tug. Before he even realized they were off she had him in her mouth, working at him like a pro.
Yuu found himself unable to speak from the sensation of the aggressive blowjob; it was the first time he had gotten more than just tentative oral. After just a minute and a half, he found himself unable to last any longer. She didn't take her mouth off for a moment as she began to swallow.
Spent, his legs gave out from under him as he sat down hard on the floor. The woman didn't waste a second as she removed her bra and began rubbing his dick between her breasts. After just a couple minutes, Yuu was ready to go again, as she quickly kicked off her panties and sat down on him.
Yuu still hadn't gotten over his surprise and couldn't bring himself to say anything, or ask who she was. It was all he could do to try and at least reciprocate, as he began touching her in ways he thought would make her feel good, before pulling himself up into a sitting position so that he could get his mouth into it.
After a few minutes, he was nearly ready to finish. She had apparently learned to read him from earlier, and pulled him out of her just before he did, rubbing him until he came on her stomach.
She stood up as Yuu tried to catch his breath. “Well, you lasted reasonably well for someone who hasn't trained, unless that was your first time in which case you lasted quite a long time,” she said. “Turnaround time is definitely not the worst I've seen. Still, there's plenty of room for improvement, especially when it comes to your fluid production. And I still have to assess your oral skills, but we can do that another time.” She quickly removed her garter belt and rolled off her stockings.
“What... just happened?” Yuu asked, as the woman walked over to the shower area. “We just had sex. If you're going to be this slow a learner, I'm going to have to ask for a raise,” the woman answered. “I know that. I mean... I guess let's start with, who are you?” Yuu tried, as she turned one of the showers on to start cleaning herself off. “I'm Yasuka Nakajou, the school's phys ed teacher. Specifically, I was hired to be your sex ed teacher, and to give you a practical education in being a skilled lover.”
“Umm... when was the last time you spoke to Nanami? I mean, I assume she's the one who hired you in the first place,” Yuu said, slightly annoyed. “Two weeks ago. I'm actually supposed to be teaching her too, but as long as she isn't here today, I figured I could at least assess where you're at, skill wise. Wait, you are Yuu, right?”
“Yes, I am,” Yuu said, trying to sort everything out in his mind, before realizing. “You weren't even sure it was me?” “It was a safe bet,” Yasuka said, rinsing herself off. “I told the rest of the class to run laps outside, and Dianne let me know why you hadn't made it out yet. And if it wasn't you, then whoever it was could just count themselves lucky to be in the right place at the right time.”
“Well, Nanami's in the hospital. And her plan's been derailed,” Yuu said. “Plan?” Yasuka asked, turning off the water and reaching for a towel. “Look, I was hired to be the school's P.E. teacher, and to be your sex ed teacher. Obviously the second part was hush hush, but the pay is good, they were willing to accept my qualifications as they are, and the extra work is simple enough. Teach one teenage boy to pleasure women? Cinch. If you don't want to, though, your sex ed grade doesn't count towards your GPA. I wouldn't mind my job becoming even easier. But I'm betting that within a week you'll be begging me to teach you.”
Yasuka got dressed and moved towards the exit. “You should get out there, though. Your gym class does count towards your GPA.”
Yuu got out to the field behind the school just a few minutes later. Yasuka was already out there, standing nearby watching everybody run laps. Yuu started to halfheartedly jog around the field, keeping an eye out for Valen and Minako. Less than a minute later, though, someone tapped him on his shoulder.
“So, I take it I'll be adding Yasuka to the list?” Cupcake asked, catching up to Yuu. “What are you implying,” Yuu asked. “There's no point in hiding it from me,” Cupcake said smugly, before continuing. “The both of you were gone for an unusually long time if it were just changing. I can smell the sex on you. And on top of that, she's a pornstar. Former pornstar now, I guess.”
“You sure about that?” Yuu asked. “I'm sure. She never let her real name slip on any of her online profiles; I probably could've called it at the beginning of the week if she had. But I definitely recognize her face. She went by the stage name 'Lisa Heart'. I could email you a playlist of her videos if you like,” Cupcake said. “... I'll pass,” Yuu said.
After another moment of jogging, Cupcake prodded at Yuu again. “Well, give me the details!” she insisted. “I'm not sure there's a lot to say about it,” Yuu said. “She told me that she was hired to be my sex ed teacher and that she was assessing me.”
“And how'd you rate?” “I'm not really sure I'm comfortable sharing this...” Yuu said. “Come on, do you want my help or not?” Cupcake carried on. “Fine,” Yuu said, rolling his eyes. “She said I lasted reasonably well for someone untrained, and that I could get it up again afterward reasonably quickly, but that I didn't make enough fluid.” Yuu turned red as he finished, regretting immediately that he shared this. “Can't say I'm surprised,” Cupcake said, barely reacting to such personal information. “In one of her interviews she did say that her bukkake videos were among her favorite.” There was an awkward silence, as Yuu struggled with how he should respond to that.
Finally Cupcake broke the silence. “Well, we'll go over it tonight. I'll be by your place at eight, so you'd better be ready.” With that, she jogged on ahead.
“... and that's what happened,” Yuu finished. After getting home he had decided to tell Valen and Minako what had happened that day. “Well... maybe it's a good thing,” Minako said. She didn't seem to be too bothered by the news. “Think about it. While I am not, by any means, disappointed by your performance, it'd be silly to think that you can't get any better. In fact, maybe we should try to get lessons from Yasuka as well! I'd love to be able to leave you a drooling mess after sex.”
“I guess that's one way of looking at it...” Yuu said, not entirely convinced. Valen, meanwhile, was giving him a scowl. “You didn't even know who she was!” she shot. “Look, I've come to terms with you having a harem. Complaining about it now would be like trying to close the barn door. But can you, just one time, try to have some control over your penis?”
“I'm sorry. But like I said, she jumped me! How often does that kind of thing actually happen in real life, really?” Yuu protested. “I'm starting to wonder, with you...” Valen said, sarcastically. “Either way, you probably should tell Mom about your teachers,” Minako said, “just because everyone should be kept aware of all your girlfriends. Keeping these things secret is the fastest way to screw this up.”
“I know, I just need to find a way to explain it to her without making her feel like she pushed me into a trap,” Yuu said. “I'm sure you'll get it figured out. Now, go get ready for that practice date with Cupcake. I'm going to start watching Oreimo. Valen, would you care to join me?” “Yeah, I can give it a shot,” Valen answered, and the two of them headed off toward the TV.
At eight o'clock, right on cue, the doorbell rang. Natsu got to the door before Yuu could. “Hello, Ms. Underwood. Is Yuu home?” “Thanks! I'll be taking it from here, Mom!” Yuu yelled as he finished hurrying to the door. “Who's your friend here? It looks like she's here for a date!” Natsu said. Cupcake had a strapless red dress on with an entirely too short flared skirt. “That's exactly it!” Cupcake said, as Yuu pulled her in the door and started leading her toward the garage.
“This is the first I've heard of it; are you one of his classmates? He did mention that it's mostly girls in there with him,” Natsu continued. “Yes, I am. My name's Cupcake, I sit right behind him,” Cupcake said cheerfully. “I'll tell you about it later,” Yuu said as he opened the door, “but we need to get going; I imagine we have a reservation we have to make?” “That's true,” Cupcake said regretfully. “But it was so nice to meet you!” she continued, smiling at Natsu. “It was nice to meet you too! Have fun you two!” Natsu said, as the two got in the car.
“Well, you're off to a terrible start,” Cupcake said. “Don't try to keep your date from making small talk with someone else; especially when they're making small talk with another woman that they're going to be sharing a dick with. Also, you didn't get my door for me.”
“I'm sorry. I'd have preferred to pick you up. Why did you come over here? It just seems like an extra step when I could've picked you up and driven straight to the restaurant,” Yuu asked. “Let's just say that it was a lot easier than trying to give you directions to where I live. Now, here are the directions to the restaurant, and we'll see if I can teach you anything.”
Yuu felt a little under dressed. While he was wearing one of his nicer outfits, most of the other men here had ties and suit coats on. “I'll take whatever cola you've got,” Yuu said to their waiter. “And for you, Ma'am?” the waiter asked. “Bring me a mojito, and keep 'em coming!” Cupcake said enthusiastically. As the waiter nodded and walked off, Yuu asked, “Wait, they're not going to card you or anything?” “Relax, they know me here,” Cupcake answered.
'Now, on to your first lesson. A date is a lot like a game of match three, where you combine three tokens of a kind to blow a load of feelings all over your date's heart...” After a moment of Yuu staring at Cupcake, she broke out laughing. “Ok, that is probably the funniest look I've ever seen someone have. Don't worry! It's just a joke!” Yuu smiled nervously, not entirely sure he understood the joke she was trying to make. “Don't worry, something tells me that someday you'll think that was hilarious,” Cupcake continued.
After an awkward moment of silence, Cupcake spoke up. “I've broken the ice for you, now this is the part of the date where you try to get to know me better...” she tried leading on. After another moment she blurted out, “So ask me!” “I'm sorry! I'm not good at this! There's a reason that everybody I've gone out with is somebody I've known most of my life!” Yuu protested.
“Here, let me give you a great example question,” Cupcake said, mildly irritated. “I know you're into blank, but that can't be your only interest. What are some of your other interests?”
“Okay,” Yuu said. “Here goes. I know you're into porn, but that can't be your only interest. What are some of your other interests?” Cupcake smiled and answered, “Well, I like to think of myself as an artist. I spend most of my time in class doodling. Maybe I should show you sometime.” “I'd be interested in seeing. I've always wanted to be able to draw but I've never had any talent,” Yuu said.
The waiter arrived with their drinks, and took their dinner orders. As he left, Cupcake continued on. “Drawing is nice and all, but even more than that I like to think of myself as an artist when it comes to dancing. I don't have a lot of use for most formal dancing, but there's not much that's sexier than a good tango. Except maybe a proper pole dance. And ballet is good for the muscle strength you get out of it. Do you know how to dance?”
“Two left feet,” Yuu answered. “Well, I'll have to teach you sometime. You might find it to be a valuable skill. Do you do anything artistic at all?” Cupcake asked. “Well...” Yuu hesitated. “I'm in a band. Really, it's Minako's band, she's the one who got everyone together. It's because we did a lot of sing-alongs together when we were younger.”
“Well, tell me about it. It might just make my job easier,” Cupcake asked. “Well... all of us in the band play characters. It kind of follows the same idea as some of the other costumed bands we've seen, like the Aquabats, and that old movie Bill & Ted; the idea that you're a band of rockstar superheroes. My character is the self proclaimed world's greatest lover. Whether or not it's true depends on whichever is funnier for that particular song. We've got two people for keyboards, one for drums, one for bass, and one player on guitar. We'd kind of like a second for guitar so we've got lead and rhythm. And then Minako's on female vocals. She hasn't made her character up yet."
“So you're vocals then, huh? Sing me one of your songs then,” Cupcake said. “Right here?” Yuu stammered. “Of course! I mean, you guys do write your own songs, right?” Cupcake asked. “We do some covers, but yeah, we write our own songs. But... we're kind of in the middle of a restaurant.” “Don't be self-conscious. Has your band ever played in front of a crowd before?”
“Not yet...” Yuu said. “Well, there's a first for everything. You're going to have to get over the idea of everyone staring at you if you ever want to do anything with this band,” Cupcake said. “Yeah, but there's a difference,” Yuu tried. “People who come to a show are expecting you to sing. Random people at a restaurant are not.”
Suddenly, Cupcake stood up in her chair. “Attention everyone!” Cupcake shouted. “My date here is going to sing me an original song by his band!” Cupcake sat back down and smiled at Yuu. “All eyes are on you, stud. Make the most of it.”
Yuu had already begun sweating buckets. “Just pretend I'm the only one in the room,” Cupcake tried, helpfully. Yuu tried calling up his experiences in middle school drama to try and block everyone but Cupcake from his mind.
Suddenly, the words he had heard in a dream years ago rang loud and clearly in his mind.
You step on stage and they come alive
No one cares that you're thirty-five
You're a rock star!
On a centaur!
You're still a nerdy kid inside
But now you've finally found your tribe
Hear the crowd roar!
Give 'em what they came for!
Suddenly, in Yuu's mind it was only him and Cupcake in the room. After taking a moment to set the tune in his head, he started on the spoken introduction to one of the ones they had finished recently.
“Why hello there. You're a very attractive young lady.
I'd like to ask you out on the hottest of dates.
I see that you have a lot of other gentlemen suitors.
Allow me to make my case.”
From there, the song proceeded as the singer tries bragging about his accomplishments to try and convince this girl to take him home with her after the party, centering primarily on a ridiculously exaggerated story of him slaying a dragon. At the end of the song, she decides to take everyone home with her, including people who weren't even at the party and everyone in the band, except the singer.
As soon as he finished, Cupcake began applauding. Throughout the rest of the room, there was sporadic applause. Yuu suddenly felt a wave of embarrassment wash over him. Cupcake reached over to reassure him. “Look, I'm not the only one clapping. You did good. For a spontaneous performance with no backup music, in a restaurant, this is a pretty good reaction. Love the humor, that's going to go over well with the other girls.”
“So, what else do you do when you're not busy fucking pornstars?” Cupcake asked. The waiter returned with their meals, and the two continued to talk as they ate.
The waiter took Yuu and Cupcake's empty plates away, and returned with more drinks. “Now see? That wasn't so hard,” Cupcake said. “You've at least got the basics of a decent date down. So now, let's work on our strategy.”
“Our strategy?” Yuu asked. “Yeah,” Cupcake said. “To get the all the other girls in class to join your harem. Fortunately, you've got the ball rolling with over half of them already; you've got a rapport already with Megumi and Erina, plus you were approached today by Ami and Manami, so what is apparently the hard part is already done with them. Factor in Valen, Minako, Nanami, and myself, and you're at over half the class. Oh yeah, plus Melissa came over to speak to you Tuesday.”
“Okay, what are your thoughts?” Yuu asked. “Well, I tried speaking to Megumi yesterday while you were out. It wasn't very productive. I gotta say, that's such a waste; that pair of tits wasted on that personality. Even so, I think she's the one to focus on first. Yesterday evening I browsed through her porn collection – don't ask me how – and what I found was mostly CG sets from Japanese games. I had to find a resource online to cross reference it to get some of the categories, though obviously not all of them. The largest category of it was gay porn.”
“So... she's a lesbian?” Yuu asked. “No, like dudes on dudes. While I'm really sure she's at least somewhat attracted to women based on what I saw, she definitely loves the d. But anyhow, I'm getting sidetracked. The second largest category was tentacles, which still doesn't help us. But the next two categories were incest and harem. Which brings me to my idea for a plan. We'll need Minako's cooperation, but I'm pretty sure she'll offer it willingly.”
After Cupcake had finished detailing her plan, she added, “One more thing. I'm about to ask you to break the cardinal rule of a good date. Pull out your cellphone.” Yuu pulled his phone out of his pocket, and Cupcake snatched it away for a moment. When she gave it back, there was a new app on his screen. “It's an app I wrote,” Cupcake said. “It's basically a database of important dates, preferences, and interests for the girls in class, that I'm going to fill out as we learn them. Just make sure that you don't check it in the middle of a date or while you're talking to them, it'll come off poorly. And try not to come off as a creepy stalker by spouting off things about them that they haven't talked to you about yet.”
Yuu pulled into the garage and took a deep breath before getting out of the car. Cupcake had had him leave her at the restaurant when they were done; she again said it was easier for her to get home that way. He made his way into the house and was almost tackled by Minako. “O-niii-saaaan!” she shouted as she grabbed him. Yuu gave a subdued chuckle. “I take it you're really liking Oreimo?” he asked. “I think it's my new favorite series, I've binge watched almost half of it now! Come watch it with me!” she said, excitedly.
“It's been a very long day, I think I'm done for the night; but I promise I'll watch it with you sometime,” Yuu said, before kissing Minako on the forehead. “Okay,” Minako said, disappointed. “Did Valen already go home?” Yuu asked. “Yeah, she left about an hour ago,” Minako answered. “Alright then. Good night,” Yuu said. “Good night!” she called out as she headed back to the TV, and Yuu headed off to his room.
Next Entry: Saturday, September 10th, 2016
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